The focus of this paper is on counterfactual narratives and whether they can be used as a learning tool in a business setting to enhance systemic thinking. Counterfactuals have recently received a lot of attention from academics of different disciplines – from politics and international relations to philosophy and management. However, little attention has been paid to evaluating the outcomes of the use of counterfactuals and whether they can be used to increase decision makers’ systemic reasoning skills and their ability to deal with the complexities of the business world. Hence this paper will discuss how counterfactuals can be used to expose deterministic worldviews and to encourage managers’ explorations of alternative scenarios of the past. The discussion of theory in this paper is complemented with the description of a PhD project, still being designed, that aims to evaluate the impact of counterfactuals on managerial awareness. The research is essentially systemic in nature, given its focus on holistic understanding and appreciation of complexity. The field work will be based around executive education-style sessions involving the analysis of a fictional case study with multiple points of intervention. In addition, the project will also aim to determine whether there is an intercultural aspect to counterfactuals and management learning, as it will involve fieldwork in Turkey, Ukraine, the Netherlands and the UK.